Beyond Rule-of-five: Permeability Assessment of Semipeptidic Macrocycles

Steering New Drug Discovery Campaigns: Permeability, Solubility, and Physicochemical Properties in the bRo5 Chemical Space

(2021) Giulia Caron et al.   ACS Medicinal Chemistry Letters

Modulation of the Passive Permeability of Semipeptidic Macrocycles: N- and C-Methylations Fine-Tune Conformation and Properties

(2021) Christian Comeau et al.   JOURNAL OF MEDICINAL CHEMISTRY

Effect of Flexibility, Lipophilicity, and the Location of Polar Residues on the Passive Membrane Permeability of a Series of Cyclic Decapeptides

(2021) Shuzhe Wang et al.   JOURNAL OF MEDICINAL CHEMISTRY

Cyclosporin Structure and Permeability: From A to Z and Beyond

(2021) Karen M. Corbett et al.   JOURNAL OF MEDICINAL CHEMISTRY

Solution conformations explain the chameleonic behaviour of macrocyclic drugs

(2020) Emma Danelius et al.   CHEMISTRY-A EUROPEAN JOURNAL

Structure-Permeability Relationship of Semi-Peptidic Macrocycles – Understanding and Optimizing Passive Permeability and Efflux Ratio

(2020) Antoine Le Roux et al.   JOURNAL OF MEDICINAL CHEMISTRY

Membrane Permeability in Cyclic Peptides is Modulated by Core Conformations

(2020) Flaviu Cipcigan et al.   Journal of Chemical Information and Modeling

Predicting the Permeability of Macrocycles from Conformational Sampling – Limitations of Molecular Flexibility

(2020) Vasanthanathan Poongavanam et al.   JOURNAL OF PHARMACEUTICAL SCIENCES

Drug–Membrane Permeability across Chemical Space

(2019) Roberto Menichetti et al.   ACS Central Science

Conformation and Permeability: Cyclic Hexapeptide Diastereomers

(2019) Satoshi Ono et al.   Journal of Chemical Information and Modeling

Why Some Targets Benefit from beyond Rule of Five Drugs

(2019) Megan Egbert et al.   JOURNAL OF MEDICINAL CHEMISTRY

Permeability of Cyclic Peptide Macrocycles and Cyclotides and Their Potential as Therapeutics

(2019) Spiros Liras et al.   ACS Medicinal Chemistry Letters

Inhibitors of protein–protein interactions (PPIs): an analysis of scaffold choices and buried surface area

(2018) Xu Ran et al.   CURRENT OPINION IN CHEMICAL BIOLOGY

Impact of Dynamically Exposed Polarity on Permeability and Solubility of Chameleonic Drugs Beyond the Rule of 5

(2018) Matteo Rossi Sebastiano et al.   JOURNAL OF MEDICINAL CHEMISTRY

Improving the Cell Permeability of Polar Cyclic Peptides by Replacing Residues with Alkylated Amino Acids, Asparagines, and d-Amino Acids

(2018) Laura K. Buckton et al.   ORGANIC LETTERS

Two Decades under the Influence of the Rule of Five and the Changing Properties of Approved Oral Drugs

(2018) Michael D. Shultz   JOURNAL OF MEDICINAL CHEMISTRY

Lipophilic Permeability Efficiency Reconciles the Opposing Roles of Lipophilicity in Membrane Permeability and Aqueous Solubility

(2018) Matthew R. Naylor et al.   JOURNAL OF MEDICINAL CHEMISTRY

Cyclic Peptides: Promising Scaffolds for Biopharmaceuticals

(2018) Donghyeok Gang et al.   Genes

Beyond the Rule of 5: Lessons Learned from AbbVie’s Drugs and Compound Collection

(2017) David A. DeGoey et al.   JOURNAL OF MEDICINAL CHEMISTRY

Determination of the pKa of the N-terminal amino group of ubiquitin by NMR

(2017) Alain Oregioni et al.   Scientific Reports

Quantifying the chameleonic properties of macrocycles and other high-molecular-weight drugs

(2016) Adrian Whitty et al.   DRUG DISCOVERY TODAY

Structural and conformational determinants of macrocycle cell permeability

(2016) Björn Over et al.   Nature Chemical Biology

Stereochemistry Balances Cell Permeability and Solubility in the Naturally Derived Phepropeptin Cyclic Peptides

(2016) Joshua Schwochert et al.   ACS Medicinal Chemistry Letters

1H and 15N NMR Characterization of the Amine Groups of Heparan Sulfate Related Glucosamine Monosaccharides in Aqueous Solution

(2015) Consuelo N. Beecher et al.   ANALYTICAL CHEMISTRY

Enantiomeric Cyclic Peptides with Different Caco-2 Permeability Suggest Carrier-Mediated Transport

(2015) Udaya Kiran Marelli et al.   CHEMISTRY-A EUROPEAN JOURNAL

Beyond cyclosporine A: conformation-dependent passive membrane permeabilities of cyclic peptide natural products

(2015) Christopher L Ahlbach et al.   Future Medicinal Chemistry

Probing the Physicochemical Boundaries of Cell Permeability and Oral Bioavailability in Lipophilic Macrocycles Inspired by Natural Products

(2015) Andrew T. Bockus et al.   JOURNAL OF MEDICINAL CHEMISTRY

Going Out on a Limb: Delineating The Effects of β-Branching, N-Methylation, and Side Chain Size on the Passive Permeability, Solubility, and Flexibility of Sanguinamide A Analogues

(2015) Andrew T. Bockus et al.   JOURNAL OF MEDICINAL CHEMISTRY

Cell-Permeable Cyclic Peptides from Synthetic Libraries Inspired by Natural Products

(2015) William M. Hewitt et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Macrocycles: lessons from the distant past, recent developments, and future directions

(2015) Andrei K. Yudin   Chemical Science

Improving on Nature: Making a Cyclic Heptapeptide Orally Bioavailable

(2014) Daniel S. Nielsen et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

pH-dependent random coil 1H, 13C, and 15N chemical shifts of the ionizable amino acids: a guide for protein pK a measurements

(2014) Gerald Platzer et al.   JOURNAL OF BIOMOLECULAR NMR

Impact of Stereospecific Intramolecular Hydrogen Bonding on Cell Permeability and Physicochemical Properties

(2014) Björn Over et al.   JOURNAL OF MEDICINAL CHEMISTRY

Cyclic Penta- and Hexaleucine Peptides without N-Methylation Are Orally Absorbed

(2014) Timothy A. Hill et al.   ACS Medicinal Chemistry Letters

P-glycoprotein ABCB1: a major player in drug handling by mammals

(2013) Piet Borst et al.   JOURNAL OF CLINICAL INVESTIGATION

Cyclic Peptides as Therapeutic Agents and Biochemical Tools

(2012) Sang-Hoon Joo   Biomolecules & Therapeutics

Small-Molecule Inhibitors of Protein-Protein Interactions: How to Mimic a Protein Partner

(2012) David C. Fry   CURRENT PHARMACEUTICAL DESIGN

Optimizing PK properties of cyclic peptides: the effect of side chain substitutions on permeability and clearance

(2012) Arthur C. Rand et al.   MedChemComm

On-resin N-methylation of cyclic peptides for discovery of orally bioavailable scaffolds

(2011) Tina R White et al.   Nature Chemical Biology

Expanding the range of ‘druggable’ targets with natural product-based libraries: an academic perspective

(2010) Renato A Bauer et al.   CURRENT OPINION IN CHEMICAL BIOLOGY

MultipleN-Methylation of MT-II Backbone Amide Bonds Leads to Melanocortin Receptor Subtype hMC1R Selectivity: Pharmacological and Conformational Studies

(2010) Lucas Doedens et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Coexistence of passive and carrier-mediated processes in drug transport

(2010) Kiyohiko Sugano et al.   NATURE REVIEWS DRUG DISCOVERY

N-Methylation of Peptides: A New Perspective in Medicinal Chemistry

(2008) Jayanta Chatterjee et al.   ACCOUNTS OF CHEMICAL RESEARCH

Improving Oral Bioavailability of Peptides by Multiple N-Methylation: Somatostatin Analogues

(2008) Eric Biron et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

The exploration of macrocycles for drug discovery — an underexploited structural class

(2008) Edward M. Driggers et al.   NATURE REVIEWS DRUG DISCOVERY

Estimating the size of the human interactome

(2008) M. P. H. Stumpf et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA